Herein, a palladium-catalyzed diastereoselective dearomatization/cross-coupling cyclization reaction between -arylacyl indoles and ()-β-chlorovinyl ketones is reported. Through this cyclization/cycloisomerization cascade, a series of furan-containing indolines were obtained in yields up to 95%. The reaction features readily accessible starting materials, benzyl Pd(II)-catalyzed cycloisomerization of ()-β-chlorovinyl ketones, the sequential formation of three bonds and bis-heterocycles, and excellent diastereoselectivity. More importantly, the carbene-secondary benzyl migratory insertion is proven to be a critical process in the sequential cyclizations.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.4c00196 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Visible-Light-Catalyzed Fast Synthesis of 1,4-Benzoxazepine Derivatives from 2-Alkoxyarylaldehydes and -Arylglycines.
J Org Chem
January 2025
Jiangxi Province Key Laboratory of Functional Organic Polymers, East China University of Technology, Nanchang 330013, China.
A novel photocatalytic method for the synthesis of 1,4-benzoxazepine using 2-alkoxyarylaldehyde as an oxygen source and -arylglycine as a nitrogen source has been reported. This method is mild, efficient, and fast, and the corresponding reaction can be completed within 2 h at room temperature under a nitrogen atmosphere and light-irradiation conditions. Mechanistic studies have confirmed that this scheme involves the decarboxylation cyclization of -arylglycine and provides a convenient pathway for the preparation of various 2-alkyl--phenyl-substituted 1,4-benzoxazepine.
View Article and Find Full Text PDFBioinspired concise synthesis of caged Sesquiterpenoids Artatrovirenols A and B.
Nat Commun
January 2025
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, Gansu, PR China.
Artatrovirenols A and B are two newly isolated sesquiterpenoids with a complex caged framework. We report herein a concise synthesis of artatrovirenols A and B in 9 and 8 steps, respectively. The complex caged tetracycle is rapidly constructed from a known planar guaiane-type precursor through a bioinspired intramolecular [4 + 2] cyclization to firstly access artatrovirenol B, which is further transformed into artatrovirenol A through a biomimetic epoxidation-mediated lactonization reaction.
View Article and Find Full Text PDFGeneral (hetero)polyaryl amine synthesis via multicomponent cycloaromatization of amines.
Nat Commun
January 2025
State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry and Chemical Engineering, Hunan University, Changsha, China.
(Hetero)polyaryl amines are extensively prevalent in pharmaceuticals, fine chemicals, and materials but the intricate and varied nature of their structures severely restricts their synthesis. Here, we present a selective multicomponent cycloaromatization of structurally and functionally diverse amine substrates for the general and modular synthesis of (hetero)polyaryl amines through copper(I)-catalysis. This strategy directly constructs a remarkable range of amino group-functionalized (hetero)polyaryl frameworks (194 examples), including naphthalene, binaphthalene, phenanthren, benzothiophene, dibenzothiophene, benzofuran, dibenzofuran, quinoline, isoquinoline, quinazoline, and others, which are challenging or impossible to obtain using alternative methods.
View Article and Find Full Text PDFSynthesis of Polysubstituted Benzo[][1,5]naphthyridine via Mn(III)-Mediated Domino Cascade Reactions of Cyclopropanols and 2-(2-Isocyanophenyl)acetonitriles.
Org Lett
January 2025
Institute of Next Generation Matter Transformation, College of Material Sciences Engineering at Huaqiao University, 668 Jimei Boulevard, Xiamen, Fujian 361021, China.
Domino cascade reactions, which can construct multiple bonds in one pot, are efficient methods to synthesize N-heterocycles and other useful skeletons. Herein, we report an expedient synthesis of polysubstituted benzo[][1,5]naphthyridine via Mn(III)-mediated C-C bond cleavage of cyclopropanols. These reactions were initiated by addition of β-carbonyl radicals, generated from cyclopropyl alcohols in the presence of Mn(III), to 2-(2-isocyanophenyl)acetonitriles to give quinolin-3-amines, which went through intramolecular cyclizations and dehydrogenation to give the final products.
View Article and Find Full Text PDFConstruction of benzimidazole- and indole-fused azabicyclo[3.1.0]hexanes bearing a cyano-containing quaternary center from vinylsulfonium salts through sequential [3 + 2]/[2 + 1] cyclization.
Org Biomol Chem
January 2025
Department of Chemistry, College of Sciences, Tianjin University of Science and Technology, Tianjin 300457, People's Republic of China.
A sequential [3 + 2]/[2 + 1] annulation reactions of benzimidazole- and indole-derived acrylonitriles with vinylsulfonium salts have been developed for the first time, and shown to provide in yields of 32 to 98% a series of azabicyclo[3.1.0]hexanes containing each a cyano-substituted tetrasubstituted carbon stereocenter with >20 : 1 dr.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!